Tetrahydroisoquinoline (THIQ) derivatives stand out as a promising class of compounds due to their diverse range of biological activities, making them particularly valuable in drug discovery. To enhance their structural diversity, an Rh-catalyzed denitrogenative annulation method has been introduced for synthesizing these derivatives. An intriguing aspect of this method is the ability of the Brønsted acid to prevent further annulation while facilitating the production of the desired THIQ derivatives, achieving impressive yields of up to 86%. This synthetic approach was subsequently leveraged to create an analogue of cyclocelabenzine, a compound showing potential as an anti-inflammatory agent.